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Showing NP-Card for 4-(2-Furanyl)-3-buten-2-one (NP0047558)

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Record Information
Version2.0
Created at2022-03-17 20:42:08 UTC
Updated at2025-07-17 01:04:44 UTC
NP-MRD IDNP0047558
Natural Product DOIhttps://doi.org/10.57994/2858
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-(2-Furanyl)-3-buten-2-one
Description4-(2-Furanyl)-3-buten-2-one, also known as monofurfurylideneacetone or furfural acetone, belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. 4-(2-Furanyl)-3-buten-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-(2-Furanyl)-3-buten-2-one is a sweet, balsam, and cinnamon tasting compound. Outside of the human body, 4-(2-Furanyl)-3-buten-2-one has been detected, but not quantified in, alcoholic beverages and coffee and coffee products. This could make 4-(2-furanyl)-3-buten-2-one a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047558 (4-(2-Furanyl)-3-buten-2-one)


  Mrv0541 05061306562D          

 10 10  0  0  0  0            999 V2000
   -1.5757    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  2  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
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3D MOL for NP0047558 (4-(2-Furanyl)-3-buten-2-one)

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3D SDF for NP0047558 (4-(2-Furanyl)-3-buten-2-one)

  Mrv0541 05061306562D          

 10 10  0  0  0  0            999 V2000
   -1.5757    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  2  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047558

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C/C1=CC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O2/c1-7(9)4-5-8-3-2-6-10-8/h2-6H,1H3/b5-4-

> <INCHI_KEY>
GBKGJMYPQZODMI-PLNGDYQASA-N

> <FORMULA>
C8H8O2

> <MOLECULAR_WEIGHT>
136.1479

> <EXACT_MASS>
136.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.16947324304736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z)-4-(furan-2-yl)but-3-en-2-one

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.5259584266666661

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.609907190710402

> <JCHEM_PKA_STRONGEST_BASIC>
-3.050394274062953

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
39.001900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-4-(furan-2-yl)but-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047558 (4-(2-Furanyl)-3-buten-2-one)
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PDB for NP0047558 (4-(2-Furanyl)-3-buten-2-one)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.941   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    6                                                       
CONECT    3    2    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    2   10                                                       
CONECT    7    1    4    9                                                  
CONECT    8    3    5   10                                                  
CONECT    9    7                                                            
CONECT   10    6    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0047558 (4-(2-Furanyl)-3-buten-2-one)
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SMILES for NP0047558 (4-(2-Furanyl)-3-buten-2-one)
CC(=O)\C=C/C1=CC=CO1
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INCHI for NP0047558 (4-(2-Furanyl)-3-buten-2-one)
InChI=1S/C8H8O2/c1-7(9)4-5-8-3-2-6-10-8/h2-6H,1H3/b5-4-
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View in JSmol
Synonyms
ValueSource
(3E)-4-(2-Furyl)-3-buten-2-oneHMDB
1-(2-Furyl)but-2-en-3-oneHMDB
2-(3-Oxobutenyl)furanHMDB
2-FuralacetoneHMDB
2-FurfurylideneacetoneHMDB
2-Furfurylideneacetone polymerHMDB
3-Buten-2-one, 4-(2-furanyl)-, homopolymerHMDB
3-Buten-2-one, 4-(2-furanyl)-, polymersHMDB
3-Buten-2-one, 4-(2-furyl)- (6ci,8ci)HMDB
3-Buten-2-one, 4-(2-furyl)-, polymersHMDB
3-Buten-2-one, 4-(2-furyl)-, polymers (8ci)HMDB
4-(2-Furanyl)-3-butene-2-oneHMDB
4-(2-Furyl)-3-buten-2-oneHMDB
4-(2-Furyl)but-3-en-2-oneHMDB
beta -2-FurylideneacetoneHMDB
Fam (monomer)HMDB
Fam polymerHMDB
FEMA 2495HMDB
Furfural acetoneHMDB
FurfuralacetoneHMDB
Furfuralacetone polymerHMDB
Furfuryl acetoneHMDB
Furfurylidene acetone polymerHMDB
FurfurylideneacetoneHMDB
Furfurylideneacetone resinHMDB
MonofurfurylideneacetoneHMDB
Monomer famHMDB
Oramin RHMDB
Oramin special GRHMDB
Poly(monofurfurylideneacetone)HMDB
PolyfurfurylidineacetoneHMDB
trans-FurfurylideneacetoneHMDB
Monofurfurylidene acetoneMeSH
Chemical FormulaC8H8O2
Average Mass136.1479 Da
Monoisotopic Mass136.05243 Da
IUPAC Name(3Z)-4-(furan-2-yl)but-3-en-2-one
Traditional Name(3Z)-4-(furan-2-yl)but-3-en-2-one
CAS Registry Number623-15-4
SMILES
CC(=O)\C=C/C1=CC=CO1
InChI Identifier
InChI=1S/C8H8O2/c1-7(9)4-5-8-3-2-6-10-8/h2-6H,1H3/b5-4-
InChI KeyGBKGJMYPQZODMI-PLNGDYQASA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600.13371 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.13371, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2025-07-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassHeteroaromatic compounds  
Sub ClassNot Available
Direct ParentHeteroaromatic compounds  
Alternative Parents
Substituents
  • Heteroaromatic compound
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Furan
    • 

  • Enone
    • 

  • Acryloyl-group
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.42ALOGPS
logP1.53ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)19.61ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033128  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011129  
KNApSAcK IDNot Available
Chemspider ID1266398  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549522  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References